1-(4-氨基苯基)-4-甲基-7,8亚甲基二氧-5H-2,3-苯并二氮杂卓盐酸盐 | 102771-26-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 中文名称: 1-(4-氨基苯基)-4-甲基-7,8亚甲基二氧-5H-2,3-苯并二氮杂卓盐酸盐
• 英文名称: 1-(4-aminophenyl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine
• 英文别名: GYKI 52466；GYKI52466；4-(8-methyl-9H-1,3-dioxa-6,7-diaza-cyclohepta[f]inden-5-yl)-phenylamine；4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine；4-(8-methyl-9H-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl)aniline
• CAS: 102771-26-6
• 化学式: C₁₇H₁₅N₃O₂
• 分子量: 293.325
• InChiKey: LFBZZHVSGAHQPP-UHFFFAOYSA-N

物化性质

• 沸点：
  472.8±45.0 °C(Predicted)
• 密度：
  1.39
• 溶解度：
  二甲基亚砜：0.39 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  69.2
• 氢给体数：
  1
• 氢受体数：
  5

制备方法与用途

GYKI 52466是红藻氨酸和AMPA激活电流的有效拮抗剂（IC50值分别为7.5 μM和11 μM），可用于研究包括帕金森病在内的神经系统疾病。

反应信息

• 作为反应物：
  描述：

  1-(4-氨基苯基)-4-甲基-7,8亚甲基二氧-5H-2,3-苯并二氮杂卓盐酸盐 在 盐酸 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以83%的产率得到GYKI 52895
  参考文献：
  名称：

  A SIMPLE AND EFFICIENT SYNTHESIS OF GYKI 52466 AND GYKI 52895

  摘要：

  The synthesis of 1-(4-aminophenyl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine (GYKI 52466. 1), the prototype of a series of noncompetitive AMPA receptor antagonists, and its 3,4-dihydroderivative (GYKI 52895, 2) is described. The title compounds have been prepared starting from safrole through a quite effective procedure.

  DOI：

  10.1081/scc-120002397
• 作为产物：
  描述：

  alpha-甲基-1,3-苯并二氧代-5-乙醇 在 phosphorus pentoxide 、 一水合肼 、 pyridinium chlorochromate 、 tin(ll) chloride 作用下， 以 乙醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 11.0h， 生成 1-(4-氨基苯基)-4-甲基-7,8亚甲基二氧-5H-2,3-苯并二氮杂卓盐酸盐
  参考文献：
  名称：

  A SIMPLE AND EFFICIENT SYNTHESIS OF GYKI 52466 AND GYKI 52895

  摘要：

  The synthesis of 1-(4-aminophenyl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine (GYKI 52466. 1), the prototype of a series of noncompetitive AMPA receptor antagonists, and its 3,4-dihydroderivative (GYKI 52895, 2) is described. The title compounds have been prepared starting from safrole through a quite effective procedure.

  DOI：

  10.1081/scc-120002397

文献信息

• N-acyl-2,3-benzodiazepine derivatives and a method of treating spasms of
  申请人：Gyogyszerkutato Intezet Kv.

  公开号：US05521174A1

  公开（公告）日：1996-05-28

  The invention relates to novel N-acyl-2,3-benzodiezapine derivatives and a method of treating spasms of the skeletal musculature therewith.

  这项发明涉及新颖的N-酰基-2,3-苯并二氮杂平衍生物及其治疗骨骼肌肉痉挛的方法。
• N-acyl-2,3-benzodiazepine derivatives, pharmaceutical compositions
  申请人：Gyogyszerku-tato Intezet Kft

  公开号：US05459137A1

  公开（公告）日：1995-10-17

  The invention relates to novel N-acyl-2,3-benzodiezapine derivatives of the general formula (I), their stereoisomers and acid-addition salts, pharmaceutical compositions containing them and a process for their preparation. In the general formula (I), defined in the specification, a more complete description of the compounds may be found. The compounds of the general formula (I) possess valuable central nervous system effects, particularly muscle-relaxant, anticonvulsive and neuroprotective action. Thus, they may be useful for the treatment of various diseases of central nervous system origin.

  这项发明涉及一种新颖的N-酰基-2,3-苯并二氮杂平衍生物，其一般式为（I），它们的立体异构体和酸盐，含有它们的药物组合物以及它们的制备方法。在一般式（I）中，根据规范定义，可以找到化合物的更完整描述。一般式（I）的化合物具有有价值的中枢神经系统效应，特别是肌肉松弛、抗惊厥和神经保护作用。因此，它们可能对治疗各种中枢神经系统起源的疾病有用。
• Novel substituted 2,3-benzodiazepine derivatives
  申请人：——

  公开号：US20040152693A1

  公开（公告）日：2004-08-05

  The invention relates to new 2,3-benzodiazepine derivatives of formula (I), isomers and acid addition salts thereof and to pharmaceutical compositions containing the same, as well as to pharmaceutical compositions and methods of using the same suitable for treating conditions associated with muscle spasms, epilepsy, acute and chronic forms of neurodegenerative diseases as well as preventing, treating or alleviating the symptoms of acute and chronic inflammatory disorders.

  这项发明涉及新的2,3-苯二氮杂环衍生物的公式(I)，其异构体和酸盐，以及含有它们的药物组合物，以及适用于治疗与肌肉痉挛、癫痫、急性和慢性神经退行性疾病相关症状的药物组合物和使用方法，以及预防、治疗或缓解急性和慢性炎症性疾病症状的方法。
• N-acyl-2,3-benzoidazepine derivatives, pharmaceutical compositions
  申请人：Gyogyszerkutato Intezet

  公开号：US05519019A1

  公开（公告）日：1996-05-21

  The invention relates to novel N-acyl-2,3-benzodiezapine derivatives of the general formula (I), their stereoisomers and acid-addition salts, pharmaceutical compositions containing them and a process for their preparation. In the general formula (I) R stands for a C.sub.1-6 alkanoyl group optionally substituted by a methoxy, cyano, carboxyl, amino, C.sub.1-4 alkylamino, di(C.sub.1-4 alkyl)amino, pyrrolidino, phthalimido or phenyl group, or by one or more halogen(s); or R is a benzoyl, cyclopropanecarbonyl, C.sub.1-5 alkylcarbamoyl or phenylcarbamoyl group; or R is absent when a double bond exists between the N(3) and C(4) atoms; R.sup.1 means hydrogen; or R.sup.1 is absent when a double bond exists between the N(3) and C(4) atoms; R.sup.2 means a C.sub.1-3 alkyl group; or R.sup.1 and R.sup.2 together stand for a methylene group and no double bond is present between the N(3) and C(4) atoms; R.sup.3 means hydrogen or a C.sub.1-4 alkanoyl group; R.sup.4 represents hydrogen; a C.sub.1-6 alkanoyl group optionally substituted by a methoxy, cyano, carboxyl, amino, C.sub.1-4 alkylamino, di(C.sub.1-4 alkyl)amino, pyrrolidino, phthalimido or phenyl group or by one or more halogen(s); as well as a benzoyl, palmitoyl, cyclopropane-carbonyl, C.sub.1-5 alkylcarbamoyl or phenylcarbamoyl group; and the dotted lines represent valence bonds optionally being present, with the proviso that no double bond exists between the N(3) and C(4) atoms when both R.sup.3 and R.sup.4 stand for hydrogen. The compounds of the general formula (I) possess valuable central nervous system effects, particularly muscle-relaxant, anticonvulsive and neuroprotective action. Thus, they may be useful for the treatment of various diseases of central nervous system origin.

  该发明涉及一种新颖的N-酰基-2,3-苯并二氮杂平衍生物，其一般式为(I)，它们的立体异构体和酸盐，含有它们的药物组合物以及它们的制备方法。在一般式(I)中，R代表一个C.sub.1-6烷酰基，可选地被一个甲氧基，氰基，羧基，氨基，C.sub.1-4烷基氨基，二(C.sub.1-4烷基)氨基，吡咯烷基，邻苯二甲酰亚胺基或苯基取代，或者一个或多个卤素; 或者R是苯甲酰基，环丙烷羰基，C.sub.1-5烷基氨基甲酰基或苯基氨基甲酰基; 或者当N(3)和C(4)原子之间存在双键时，R不存在; R.sup.1代表氢; 或者当N(3)和C(4)原子之间存在双键时，R.sup.1不存在; R.sup.2代表一个C.sub.1-3烷基; 或者R.sup.1和R.sup.2一起代表一个亚甲基基团，N(3)和C(4)原子之间没有双键存在; R.sup.3代表氢或一个C.sub.1-4烷酰基; R.sup.4代表氢; 一个C.sub.1-6烷酰基，可选地被一个甲氧基，氰基，羧基，氨基，C.sub.1-4烷基氨基，二(C.sub.1-4烷基)氨基，吡咯烷基，邻苯二甲酰亚胺基或苯基或一个或多个卤素取代; 以及一个苯甲酰基，棕榈酰基，环丙烷羰基，C.sub.1-5烷基氨基甲酰基或苯基氨基甲酰基; 虚线代表可能存在的价键，但要注意的是，当R.sup.3和R.sup.4都代表氢时，N(3)和C(4)原子之间不存在双键。一般式(I)的化合物具有有价值的中枢神经系统效应，特别是肌肉松弛、抗惊厥和神经保护作用。因此，它们可能对治疗中枢神经系统起源的各种疾病有用。
• N-acyl-2,3-benzodiazepine derivatives for treating acute and chronic
  申请人：Cyogyszerkutato Intezet KFT

  公开号：US05639751A1

  公开（公告）日：1997-06-17

  The invention relates to novel N-acyl-2,3-benzodiezapine derivatives of the general formula (I), their stereoisomers and acid-addition salts, pharmaceutical compositions containing them and a process for their preparation. In the general formula (I) R stands for a C.sub.1-6 alkanoyl group optionally substituted by a methoxy, cyano, carboxyl, amino, C.sub.1-4 alkylamino, di(C.sub.1-4 alkyl)amino, pyrrolidino, phthalimido or phenyl group, or by one or more halogen(s); or R is a benzoyl, cyclopropanecarbonyl, C.sub.1-5 alkylcarbamoyl or phenylcarbamoyl group; or R is absent when a double bond exists between the N(3) and C(4) atoms; R.sup.1 means hydrogen; or R.sup.1 is absent when a double bond exists between the N(3) and C(4) atoms; R.sup.2 means a C.sub.1-3 alkyl group; or R.sup.1 and R.sup.2 together stand for a methylene group and no double bond is present between the N(3) and C(4) atoms; R.sup.3 means hydrogen or a C.sub.1-4 alkanoyl group; R.sup.4 represents hydrogen; a C.sub.1-6 alkanoyl group optionally substituted by a methoxy, cyano, carboxyl, amino, C.sub.1-4 alkylamino, di(C.sub.1-4 alkyl)amino, pyrrolidino, phthalimido or phenyl group or by one or more halogen(s); as well as a benzoyl, palmitoyl, cyclopropanecarbonyl, C.sub.1-5 alkylcarbamoyl or phenylcarbamoyl group; and the dotted lines represent valence bonds optionally being present, with the proviso that no double bond exists between the N(3) and C(4) atoms when both R.sup.3 and R.sup.4 stand for hydrogen. The compounds of the general formula (I) possess valuable central nervous system effects, particularly muscle-relaxant, anticonvulsive and neuroprotective action. Thus, they may be useful for the treatment of various diseases of central nervous system origin.

  该发明涉及一种新颖的N-酰基-2,3-苯并二氮杂平衍生物，其一般式为(I)，它们的立体异构体和酸盐，含有它们的药物组合物以及它们的制备方法。在一般式(I)中，R代表一个C.sub.1-6烷酰基，该基可选择性地被甲氧基，氰基，羧基，氨基，C.sub.1-4烷基氨基，二(C.sub.1-4烷基)氨基，吡咯烷基，邻苯二甲酰亚胺或苯基取代，或者被一个或多个卤素取代；或者R是苯甲酰基，环丙烷羰基，C.sub.1-5烷基氨基甲酰基或苯基氨基甲酰基；或者当N(3)和C(4)原子之间存在双键时，R不存在；R.sup.1代表氢；或者当N(3)和C(4)原子之间存在双键时，R.sup.1不存在；R.sup.2代表一个C.sub.1-3烷基基团；或者R.sup.1和R.sup.2一起代表一个亚甲基基团，并且N(3)和C(4)原子之间不存在双键；R.sup.3代表氢或一个C.sub.1-4烷酰基；R.sup.4代表氢；一个C.sub.1-6烷酰基，该基可选择性地被甲氧基，氰基，羧基，氨基，C.sub.1-4烷基氨基，二(C.sub.1-4烷基)氨基，吡咯烷基，邻苯二甲酰亚胺或苯基取代，或者被一个或多个卤素取代；以及一个苯甲酰基，棕榈酰基，环丙烷羰基，C.sub.1-5烷基氨基甲酰基或苯基氨基甲酰基；虚线代表可能存在的化合价键，但要注意的是，当R.sup.3和R.sup.4都代表氢时，N(3)和C(4)原子之间不存在双键。一般式(I)的化合物具有有价值的中枢神经系统效应，特别是肌肉松弛、抗惊厥和神经保护作用。因此，它们可能对治疗中枢神经系统起源的各种疾病有用。